WO2008032850A1 - Composition photopolymérisable - Google Patents

Composition photopolymérisable Download PDF

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Publication number
WO2008032850A1
WO2008032850A1 PCT/JP2007/068020 JP2007068020W WO2008032850A1 WO 2008032850 A1 WO2008032850 A1 WO 2008032850A1 JP 2007068020 W JP2007068020 W JP 2007068020W WO 2008032850 A1 WO2008032850 A1 WO 2008032850A1
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group
formula
compound
weight
parts
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PCT/JP2007/068020
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Japanese (ja)
Inventor
Kazuhiro Kojima
Raphael Lamy
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Three Bond Co., Ltd.
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Priority to EP07807424A priority Critical patent/EP2065444A4/fr
Publication of WO2008032850A1 publication Critical patent/WO2008032850A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/07—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
    • C09K2200/0647—Polyepoxides

Definitions

  • the present invention relates to a photopower thione-polymerizable composition that is polymerized and cured by irradiation with active energy rays such as ultraviolet rays. More specifically, the present invention has excellent durability such as photopolymerization (curing) property, heat resistance, moisture resistance and the like, and adhesion to various base materials such as (engineering) plastic, metal, wood, paper, glass, slate and the like.
  • the present invention relates to a liquid photothion polymerizable resin composition useful as a ring material.
  • the photo-thion polymerizable composition that initiates cationic polymerization by light irradiation is not affected by oxygen during curing, unlike the photo radical polymerizable composition, and the effective post-cure is achieved by heating after light irradiation. It is known that there are advantages such as being able to polymerize a wide variety of monomers.
  • Clivero has summarized the general idea of photopower thione polymerization (JV Crivello: Advancesin P o 1 yme r Sci en ce, Vol. 62, 1, 1984).
  • a photoacid generator is usually used as the polymerization initiator.
  • onium salts such as aromatic odonium salts and sulfonium salts have been mainly used as industrial materials.
  • sensitizers that accelerate photothion polymerization by using in combination with the photoacid generator have been reported depending on the type of initiator.
  • pigments such as acridine orange, acridine yellow, benzoflavin, and cetoflavin T
  • aromatic compounds such as perylene, pyrene, anthracene, phenothiazine, 1,2-benzacetracene, coronene, thixanthone, fluorenone, benzophenone
  • Aromatic carbonyl compounds such as anthraquinone are known.
  • Optical pickups such as CDs and DVDs, which are called optoelectronic parts, optical parts such as photocopiers, laser housings (bases) such as laser beam printers (LBP), optical molding materials 3D solid molding materials, printing plate materials, various optical elements, optical lenses, CDs, DVDs, optical discs such as Blu-ray discs, evening panels, liquid crystal, organic / inorganic EL, display elements such as electronic paper, Used in various productions such as sealants and adhesives for various types of batteries such as dye-sensitized solar cells.
  • resin compositions that can be cured not only by ultraviolet curing but also by visible light have been commercialized one after another. Has been.
  • Epoxy resin which is a representative cationic polymerizable compound, is basically known to have higher durability such as heat resistance and moisture resistance than acrylic resin, but it has photo-curing properties. Compared with, the curability is highly dependent on the ambient temperature, for example, it takes a long time to cure at a low temperature of 15 or less, and some epoxy materials require heating after light irradiation. There was a thing. In particular, a resin composition capable of obtaining sufficient curability by an active energy ray in the visible light region has not been proposed yet. In order to solve the above-mentioned problem, Japanese Patent Application Laid-Open No. 10-2 2 6 6 5 8 proposes an acid generator in which a salt is formed by aromatic imide, sulfonium, etc.
  • JP-A-10-2 7 9 6 16 discloses a photopolymerizable composition
  • a photopolymerization initiator containing a cationic polymerizable substance, a sulfonium salt, and thixanthone. It may be useful to have a thixanthone structure It is disclosed.
  • sulfonium salts having this thixanthone structure often have low solubility in epoxy resins.
  • sulfonium salts are said to have low solubility in epoxy resins, but the addition of this thixanthone structure further reduces the solubility. Further, since this compound is bulky, it has to be added in a large amount in order to obtain sufficient curability, and there is a problem that physical properties of the cured product are impaired.
  • Japanese Patent Application Laid-Open No. 2002-40632 discloses a compound having an oxetanyl group and an epoxy group in the same molecule, a thione polymerization initiator such as sulfonium salt and danium salt, a radical polymerizable unsaturated compound, An eight-hybrid composition comprising a photo-power thione polymer resin and a photo-radical polymer resin, which comprises a photo-radical polymerization initiator, is disclosed.
  • a compound in which an oxetanyl group and an epoxy group are introduced in one molecule has been proposed, but it does not particularly contribute to improvement of photocurability.
  • JP-A-10-226658 a combination system of radical polymerization materials is also being studied, but it is insufficient from the viewpoint of extracting the performance of the epoxy resin.
  • JP-T-2001-520758 discloses a photocurable composition
  • a photoinitiator system comprising an epoxy resin, a hydroxyl-containing substance, a visible light sensitizer such as a jordanium salt and camphorquinone, and an electron donor compound.
  • JP-A-2001-0520759 discloses a photocurable composition obtained by further adding a hydroxy-containing substance to the composition of JP-T-2001-520758.
  • the hydroxy-containing materials used here are essentially free of heat and photodegradable groups and are not expected to decompose or release volatile components under typical photocuring conditions.
  • Japanese Laid-Open Patent Publication No. 1995-118369 proposes an epoxy resin blended with propylene glycol, but propylene glycol does not have a sufficient curing accelerating action, and is used as an active basic donor. Therefore, it works to delay or stop the curing.
  • the object of the present invention is to solve the above-mentioned problems of the prior art, in particular, photocuring property, particularly polymerizing and curing rapidly by irradiation with visible light (380 to 500 nm), and various physical properties of the cured product. Furthermore, it is to provide a photothermographic polymerizable composition having excellent storage stability before polymerization and curing.
  • the present invention is a.
  • R 2 and R 3 each independently represent a hydrogen atom, an alkyl group, a hydroxy group or a hydroxyalkoxy group. However, R 2 and R 3 always represent an alicyclic hydrocarbon structure. May be formed)
  • the photothion polymerizable composition of the present invention has a remarkable improvement in photocuring property, particularly the curing rate by visible light, and adheres to materials that do not like over-irradiation or irradiation itself, or materials that transmit or absorb ultraviolet rays.
  • agent, sealant, coating agent is there.
  • the photopower thione polymerizable composition of the present invention can be designed to improve photocurability, in particular, the curing rate by visible light.
  • Fig. 1 is a graph showing the ultraviolet blocking ability of an acrylic plate containing no UV absorber and an acrylic plate containing an UV absorber.
  • Examples of the cationically polymerizable compound (A) used in the present invention include conventionally known cationically polymerizable compounds such as epoxy compounds (including epoxy resins as typical examples), oxetane compounds, vinyl ether compounds, and cyclic sulfide compounds. , Cyclic amine compounds, organic silicon cyclic compounds, and the like, and epoxy compounds and oxetane compounds are preferably used.
  • An epoxy compound is a monomeric or polymeric compound containing one or more epoxy groups in the molecule, specifically, a monomer, oligomer or polymer containing one or more glycidyl groups. More specifically, for example, bisphenol A type, bisphenol F type, alicyclic epoxy resins and the like can be mentioned.
  • a resin containing chlorine-based ions such as epoxy resin synthesized using epichlorohydrin, it is preferable to add a product that has been purified by distillation, and the hydrolyzable chloride concentration is preferably The lower the better.
  • an oxetane compound is a monomeric or polymeric compound containing one or more oxetane rings in the molecule.
  • a compound having one oxetane ring in the molecule 3-ethyl 3- —Hydroxymethyloxetane, 3- (Meth) aryloxymethyl—3-Ethyloxetane, (3-Ethyl-3-oxetanylmethoxy) methylbenzene, —Fluoro [1- (3-Ethyl 3-methyl)] Benzene, 4-methoxy- [1- (3-ethyl-3-methoxy) methyl] benzene, [1- (3-ethyl-3-cetylmethoxy) ethyl] phenyl ether, isobutoxymethyl (3- Ethyl-3-oxetanyl methyl) ether, isoponyl oxetyl (3-ethyl 3- —H
  • exemplary compounds can constitute component (A) alone or in combination of two or more.
  • the acid generator (B) used in the present invention is selected from conventionally known acid generators by selecting an aromatic salt and / or an aromatic sulfone salt. Among them, a ododonium salt represented by the following general formula (5) can be preferably used. Of course, this does not preclude the use of other photocationic initiators or their combined use.
  • MX one k + 1 (Wherein and R 2 each independently represents a hydrogen atom, an alkyl group (preferably an alkyl group having 1 to 18 carbon atoms) or an alkoxy group (preferably an alkoxy group having 1 to 18 carbon atoms).
  • M represents a metal (preferably phosphorus)
  • X represents a halogen atom (preferably a fluorine atom)
  • k represents a valence of the metal
  • photo-ionic thione polymerization initiators include diphenyl rhodium, hexafluorophosphate, diphenyl rhodium, hexafluoroanmonate, diphenyl rhodium, tetrafluoro Oloporate, Diphenyl Dome, Tetrakis (Penufufluorophenyl) Polate, Bis (Dodecyl Phenyl) Jodnyum, Hexafluorophosphate, Bis (Dodecyl Phenyl) Yod Durum, Hexafluoro Antimonate, Bis (dodecylphenyl) monodonum, Tetrafluoroborate, Bis (dodecylphenyl) jodnium, Tetrakis (pentafluorophenyl) porate, 4 _Methylphenyl 4_ (1-Methylethyl) phenyl Hexa
  • the preferred blending ratio of the above-mentioned photo-based thione polymerization initiator is a photopolymerization initiator.
  • (Catalyst compound) (A) Generally, the amount of addition is sufficient to provide photocurability, but the range is generally about cationically polymerizable compound (A) 0.01 to 10.0 weight per 100 weight parts of total Addition of parts is appropriate, more preferably 0.1 to 5.0 parts by weight. If the amount is less than 0.1 parts by weight, the reaction becomes extremely slow and the reaction does not proceed sufficiently. If the amount exceeds 10.0 parts by weight, the original physical properties of the resin cannot be obtained, resulting in performance degradation. In addition, liquid storage stability before curing may be reduced. This ododonium-based photopower thione polymerization initiator is combined with The kind of the cation polymerizable compound is appropriately designed and used depending on the blending ratio or its use.
  • the benzoyl compound (C) used in the present invention is a hydroxyl group-containing benzoyl compound represented by the general formula (1), and more specifically has the following chemical structures (2) and (3). It is a hydroxyl group-containing benzoyl compound
  • R 1 R 2 and R 3 are each independently a hydrogen atom or an alkyl group (preferably an alkyl group having 1 to 18 carbon atoms, such as a methyl group or an ethyl group, more preferably 1 to 8). Represents a hydroxy group or a hydroxyalkoxy group (preferably a hydroxyalkyl group having 1 to 18, and more preferably 1 to 8, carbon atoms such as a hydroxymethoxy group or a hydroxyethoxy group).
  • the compound of the general formula (2) include 2-hydroxy-1-methyl-1-phenylpropane 1-one, 2-hydroxy-2-methyl-1-phenylbutan-1-one, 2-ethyl- 2-hydroxy-1-phenylphenyl-1-one, 1-one (4-methylphenyl) 2-hydroxy-1-2-methylpropane 1-one, 1-one (4-methylphenyl) -2-hydroxy-1-2-methylbutane 1-one, 1 _ (4 1-methylphenyl) 1 2-ethyl phthalate 2-hydroxybutane 1-one, 1— (4-ethylphenyl) 1 2-hydroxy-2-methylpropane 1 1-one, 1 1 ( 1-Hydroxyl) 1-Hydroxyl 2-Methylbutane 1 1-one, 1- (4-Ethylphenyl) 1 2-Ethyl-1-2-hydroxybutane 1-one, 1- 1 (4-Propylphenyl) _ 2—Hydroxy-1 2-me 1-one, 1-one (4-propylphenyl) 1-one,
  • Specific examples of the compound of the general formula (3) include 1-hydroxycyclohexyl-phenylmethanone, 1-hydroxycyclohexyl-1,4-methylphenylmethanone, 4-1-ethylcyclohexyl, 1-hydroxycyclohexylmethanone, 1-hydroxycyclo hexyl 4-isopropylphenylmethanone and the like can be mentioned.
  • the hydroxyl group-containing benzoyl compound (C) is added as an aid to assist the function of the acid generator (B), and the amount added is generally about 0.001 by weight per 100 parts by weight of the total amount of photothion polymerizable compounds.
  • the range of 1 part by weight is appropriate, more preferably 0.1 to 5.0 parts by weight. If the amount is less than 1 part by weight, the addition amount is too small to increase the activity of the photopolymerization initiator (B), resulting in problems such as extremely slow reaction or insufficient progress of the reaction. On the other hand, if the amount exceeds 10 parts by weight, not only an effective effect as a catalyst will not be obtained, but also the performance of the hardened material will be lowered, or the liquid storage property before curing will be lowered.
  • this Benzoreich compound is also designed and used as appropriate according to the kind and blending ratio of the cationic polymerizable compound to be combined, its use, etc., like the onion salt photopolymerization initiator.
  • the radical generator (D) used in the present invention is a thixanthone-type radical generator, and in particular, a compound represented by the following general formula (4) is preferably used.
  • each R is independently a hydrogen atom, an eight-rogen atom, or an alkyl group (preferably an alkyl group having 1 to 18 carbon atoms, such as a methyl group or an ethyl group, more preferably 1 to 8).
  • a hydroxy group or a hydroxyalkoxy group preferably a hydroxyalkyl group having 1 to 18, and more preferably 1 to 8, carbon atoms such as a hydroxymethoxy group or a hydroxyethoxy group).
  • thixanthone-type radical generator examples include 2-chlorothiaxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and isopropylthioxanthone.
  • the thixanthone-type radical generator (D) must be used in combination with the above components (B) and (C), and in particular, the curing reactivity with visible light can be enhanced.
  • the addition amount is generally appropriate to add from 0.001 to 10.0 parts by weight, more preferably from 0.1 to 5.0 parts by weight per 100 parts by weight of the total amount of the light-powered thione polymerizable compound. is there. If the amount is less than 1 part by weight, the addition amount is too small to increase the activity of the acid generator (B), so that the reaction becomes extremely slow or the reaction does not proceed sufficiently.
  • the amount exceeds 10 parts by weight, not only an effective effect as a catalyst will not be obtained, but also the performance of the hardened material will be lowered, and the liquid storage property before curing will be lowered.
  • the types and mixing ratios of the component (C) and the component (D) are appropriately designed and used depending on the application.
  • a colorant such as a pigment or a dye, calcium carbonate, talc, silica, alumina, aluminum hydroxide is used as long as the characteristics of the polymerizable composition of the present invention are not impaired.
  • Inorganic fillers such as silver, conductive particles such as silver, flame retardants, boric acid esters and phosphates, preservatives such as inorganic acids and organic acids, organic fillers such as acrylic rubber and silicon rubber, polyimide resins, General-purpose phenoxy resins such as polyamide resin, bisphenol A type phenoxy resin, bisphenol F type phenoxy resin, bisphenol A bisphenol F copolymerized phenoxy resin, polymethacrylate resin, polyacrylate resin, polyimide resin , Polyurethane resins, Polyester resins, Polyvinyl petital resin, SBS resin and Epoxy resins modified product, the polymer one or thermoplastic elastomer one SEBS resin or a modified product thereof or the like, soluble plasticizer, organic solvent, antioxidant, defoaming agent, coupling agent, leveling agent, rheology An appropriate amount of an additive such as a control agent may be blended. By these additions, a composition excellent in resin strength, adhesive strength, flame retardancy, thermal conductivity, storage
  • the photopolymerizable composition of the present invention catalyze-polymerizes component (A) by activating and interacting with components (B), (C) and (D) by irradiation with active energy rays such as ultraviolet rays.
  • the active energy line used here is an electron beam, ultraviolet light, visible light, or the like.
  • the photopolymerizable composition of the present invention exhibits a characteristic that it is effectively polymerized and cured by irradiation with light (mainly visible light) having a wavelength of 3 80 to 5 O Onm.
  • the photopolymerizable composition of the present invention is effective by providing an integrated light amount (irradiation amount) of at least 1 Om JZ cm 2 or more if the wavelength is 3800 to 500 nm. Polymerization can be cured.
  • the photopolymerizable composition of the present invention can be used in combination with a thermosetting agent that heat-cures the cationically polymerizable compound (A).
  • a thermosetting agent that heat-cures the cationically polymerizable compound (A).
  • thermosetting agent examples include Lewis acids (for example, boron trifluoride, titanium chloride, ferric chloride, ferrous chloride, ferric chloride, zinc chloride, zinc bromide, primary chloride) Tin, stannic chloride, stannous bromide, stannic bromide, dibutyl stannic dichloride, butyl stannic dibromide, tetraethyl tin, tetraptyl tin, triethyl aluminum, aluminum, jetyl aluminum chloride, Ethyl aluminum dichloride, etc.) and electron donating compounds (eg, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, hexamethylphosphoric triamide, dimethyl sulfoxide, trimethyl phosphate, phosphoric acid Complex with triethyl etc .; protonic acid (for example, halogenocarboxylic acids, sulfonic acids, sulfuric monoester,
  • thermal latent curing agents such as imidazole derivatives and organic acid dihydrazides can also be used in combination.
  • the other components (B) to (D) are mixed in any order in the cation polymerizable compound (A) in a light-shielded state.
  • -A uniform solution may be obtained by stirring. If any of the components are difficult to dissolve, the solution may be heated to such an extent that the stability of the system is not impaired.
  • the surroundings of the compounding container were shielded from light, and the photoactive thione polymerizable compound (A), photoactive thione polymerizable initiator (B), hydroxyl group-containing benzoyl compound (C), and thixanthone type radical generator (D) are listed in Table 1.
  • Table 2 a predetermined amount was blended and mixed and stirred while heating to 50 ° C. to prepare the desired light-power thione polymerizable composition.
  • other polyhydric alcohols were combined in the sense of comparing with a hydroxyl group-containing benzoyl compound, and the difference was shown.
  • the blending ratios in the table are based on weight unless otherwise specified.
  • the depth of cure was measured in mm and rounded off to two decimal places.
  • the prepared photo-curing resin is filled in a light-shielded plastic cylinder (inner diameter 5 mm, t 1 Om m) and passed through an acrylic plate (Acrypet VH O 01 ... made by Mitsubishi Rayon Co., Ltd.) containing a UV adsorbent. Similarly, after 10 seconds of irradiation (accumulated light intensity of about 3000 mJ / cm 2 ), the depth of deep curing was measured immediately.
  • Fig. 1 shows the ultraviolet blocking ability of the above-mentioned acrylic plate VH-001 and an acrylic plate containing no ultraviolet absorber (Acrypet VH-000, manufactured by Mitsubishi Rayon Co., Ltd.). table 1
  • Table 3 The symbols in Tables 1 to 3 above mean the following.
  • EP-830 Bisphenol A-type epoxy resin ... Made by Japan Epoxy Resin Co., Ltd.
  • UVR6 1 1 0 Alicyclic epoxy resin ... Dow Chemical
  • rUV I-6976J Triarylsulfonium hexafluoroantimonate ... made by Dow Chemical
  • the light-powered thione polymerizable composition containing (A) to (D) as essential components of the present invention has good light (visible light) curability for surface curability and deep curability. It can be seen that
  • the light-power thione polymerizable composition of the present invention is excellent in photocurability, durability and the like, and various substrates such as (engineering) plastic, metal, wood, paper, glass, slate, etc. Good adhesion to plastic, wood, ceramics, glass, paper and other coating materials, optical molding materials, three-dimensional solid molding materials, printing plate materials, various optical elements, optical lenses, optical disks such as CD and DVD, etc. Liquid crystal, Organic / Inorganic EL, Sealing agent for display elements, such as electronic paper, Adhesive, Sealing agent for various batteries such as dye-sensitized solar cells, Adhesive, In addition, useful as adhesive for various base materials, sealing material This is a liquid photocurable resin composition. Useful for molding optical parts such as optical pickups such as CDs and DVDs as optoelectronic parts, optical housings (bases) such as photocopiers and laser one-beam printers (LBP), and adhesive bonding of these parts. is there.
  • various substrates such as

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

L'invention concerne une composition polymérisable photo-cationique qui présente une propriété de photodurcissement si bonne que la composition peut se polymériser et durcir rapidement, dès qu'elle est irradiée par une lumière visible (380 à 500 nm), qu'elle présente d'excellentes propriétés physiques une fois durcie, et qu'elle présente une excellente stabilité de stockage avant d'être polymérisée et durcie. La composition polymérisable photo-cationique comprend essentiellement (A) 100 parties en poids d'un composé polymérisable cationique (par exemple, un composé époxy), (B) entre 0,01 et 10 parties en poids d'un générateur d'acide comprenant un sel d'iodonium aromatique et/ou un sel de sulfonium aromatique, (C) entre 0,01 et 10 parties en poids d'un composé benzoyle qui possède un groupe hydroxy et (D) entre 0,01 et 10 parties en poids d'un générateur de radicaux de type thioxanthone.
PCT/JP2007/068020 2006-09-14 2007-09-11 Composition photopolymérisable WO2008032850A1 (fr)

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EP07807424A EP2065444A4 (fr) 2006-09-14 2007-09-11 Composition photopolymérisable

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JP2006-248996 2006-09-14
JP2006248996A JP5168860B2 (ja) 2006-09-14 2006-09-14 光重合性組成物

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TWI409295B (zh) 2013-09-21

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